4.5 Article

Synthesis and Structural Characterization of a New Class of Strong Chiral Bronsted Acids: 1,1′-Binaphthyl-2,2′-bis(sulfuryl)imides (JINGLEs)

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 27, Pages 5165-5170

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000810

Keywords

Bronsted acids; Organocatalysis; Chirality; Sulfonamides; Biaryls

Funding

  1. Deutsche Forschungsgemeinschaft [SPP 1179]
  2. Fonds der Chemischen Industrie

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We herein present the first synthesis of 1,1'-binaphthy1-2,2'-bis(sulfuryl)imides (JINGLEs). This new class of chiral Bronsted acids was synthesized in one step from the corresponding BINOLs and imidobis(sulfuryl chloride). A total of six enantiopure 1,1'-binaphthyl-2,2'-bis(sulfuryl)imides, carrying different 3,3'-substituents, were synthesized and characterized, inter alia, by X-ray crystallography.

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